Hillsborough CA Real Estate, Homes, Condos for Sale

4 Beds ⋅ 3 Baths ⋅ ML81931239 MLS

This 1920's Spanish single-level home is truly magical and unique in Hillsborough! Tucked away on a mostly flat and landscaped 1.3 acre lot in the sought-after Hillsborough Oaks neighborhood, the house features an arched entry, wood-beamed ceilings and stylish character. Highlights include a living room with cathedral ceilings, custom fireplace and windows on three sides. The great room combines an updated kitchen, walk-in pantry and family room with access to the private and spectacular deck. In the bedroom wing of the home, the primary bedroom has 3 walls of windows, ensuite bathroom and walk-in closet. Take a step outside to the true oasis of a backyard including a large pool, sprawling lawns (with a well to help with the lush landscaping), patios, decks and mature landscaping. All this, and Hillsborough's famed public schools and minutes to 280 and 101.

1033 Jackling DR, Hillsborough

$3,688,000

3 Beds ⋅ 2 Baths ⋅ ML81931146 MLS

Defined by its extraordinary lot, complete privacy, and indoor/outdoor living spaces, this stunning Hillsborough property is a California dream. Situated on a flat and sun-drenched lot in lower Hillsborough, this single-story ranch-style house boasts a central hall floor plan, three bedrooms and two bathrooms, and sliding glass doors throughout that open onto the backyard. The large-scale living room and formal dining room both have picture windows and sliding glass doors that look onto different areas of the backyard. The light-filled kitchen includes a breakfast nook with a bay window. The bedrooms extend the indoor/outdoor lifestyle as they open to the yard. The impressive yard encompasses a lawn, a patio, a sizable pool, a Zen garden, and a large empty court that can be converted to another space. The property includes a horseshoe driveway and a three-car garage. All within walking distance to town, the property possesses endless potential to create the home of your dreams.

350 Crystal Springs RD, Hillsborough

$6,488,000

5 Beds ⋅ 6 Baths ⋅ ML81930613 MLS

WELCOME TO "HIDDEN VILLA"...An opportunity to tailor a stunning new modern home with all of your custom touches. Tucked down a long private drive, the seclusion is unrivaled, yet you are less than 5 minutes from Crocker Middle School, Nueva, and Highway 280. Myriad potential to augment the lifestyle with infinity pool, ADU, and outdoor Zen courtyards. The architectural design is currently all framed in, spanning 5 bedrooms, 5.5 bathrooms, plus top floor office. 10 ft. ceilings, elevator shaft ready to go, premium Fleetwood windows and doors (already installed), and much more planned. Price is for lot and progress of construction in its current state. Bring your builder or discuss partnering with the owner/contractor. Experience the heart of Hillsborough's Carolands lifestyle, adjacent to prestigious Skyfarm lands, and within 5 minutes of Hwy 280 connection, West Elementary, Crocker Middle & Nueva! Downtown Burlingame & SFO Airport within an easy 10-15 minutes:The World at your Doorstep

762 Chateau DR, Hillsborough

$3,488,000

3 Beds ⋅ 2 Baths ⋅ ML81930542 MLS

Resting on a level .52 acre lot in the desirable Carolands neighborhood is this welcoming and inviting ranch style home. Delightful curb appeal of front shutters, brick accents, & private driveway. Sun-filled living room is the perfect gathering place leading to the formal dining room. Three well-placed bedrooms include a primary with en suite bathroom. Additional multi-purpose family room or home office. The kitchen, with its new quartz countertops, opens directly onto the expansive grounds. This homes backyard paradise is wondrous. Fully landscaped with winding paths, soaring trees, thriving roses, plentiful fruit trees, green planting beds, & DIY potting shed. Quality indoor/outdoor living. Two car garage provides extra storage space with laundry. Prime luxury location! Easy access to highways 280 & 92. Nearby to scenic walking & biking trails. Close to downtown Burlingame with its cafes, trendy shops, & restaurants. Award winning schools.

1808 Black Mountain RD, Hillsborough

$4,498,000

4 Beds ⋅ 3 Baths ⋅ ML81930438 MLS

A perfect blend of traditional timeless architecture and colonial style, this residence is located in prestigious Lower Hillsborough offering curb appeal, comfort, style, and elegance. The open floor plan features a stunning entrance with a sweeping staircase leading up to the second level, a sizeable step-down living room with a beautiful fireplace, perfect for entertaining guests. The updated kitchen features modern appliances and plenty of cabinet space. The second level showcases an elegant primary suite with a beautiful view of the garden, spacious walk-in closet, and a completely renovated bathroom, making it a luxurious retreat. There are also two additional bedrooms on this level, both of which are spacious and comfortable. The top floor is a sizable 4th room offering ample natural light. The backyard features a spacious patio, a pool, and landscaped grounds. Just minutes away from shopping, restaurants, and both downtowns of Burlingame and San Mateo. This is a must see!

511 W Santa Inez AVE, Hillsborough

$4,799,800

5 Beds ⋅ 5 Baths ⋅ ML81930274 MLS

A must-see opportunity in Hillsborough! Spectacular unobstructed view of the San Mateo Bridge, city lights, the Bay and the mountains, from both 1st and 2nd floors! Enjoy the evening view in total privacy from the living room, dining room, and the master bedroom! Completely remodeled in 2011, with pool and deck renovated in 2016. This gorgeous home has been totally transformed with luxurious finishes throughout. Grandeur ceiling in foyer and living room. Modern layout with refined traditional taste. Excellent floor plan for entertaining with a half-bath on the main floor. 4 bedrooms plus home office and 4 full baths upstairs. Well-sized kitchen with high-end appliances. Minutes from Downtown San Mateo and the best shops and restaurants. Located in the heart of Silicon Valley. Easy access to Caltran, HWY 92, 280 and 101.

1025 Tournament DR, Hillsborough

$12,350,000

5 Beds ⋅ 6 Baths ⋅ ML81930175 MLS

Reimagined from top to bottom, this home has been artfully transformed inside and out into chic designer style while maintaining the original mid-century modern aesthetic. The whole-home renovation, with architecture by owner Melanie Thibault of Charlie Barnett Associates, is an absolute masterpiece with attention to detail that is second to none. White oak hardwood floors unify flowing spaces that predominantly span one level, custom cabinetry is often floating for contemporary panache, and tile and quartz selections are five-star. Ceiling heights reach 10 feet in the main living areas with entire walls of glass that invite seamless indoor/outdoor living. For more info please visit WWW.35Mccreery.com

35 Mc Creery DR, Hillsborough

$3,799,000

3 Beds ⋅ 3 Baths ⋅ ML81929566 MLS

Unlock the front door to your dreams & start making memories youll cherish forever in this extraordinary Hillsborough home. Tucked away at the end of a private cul-de-sac. Surrounded by a canopy of trees & lush greenery. Located close to 280 for smooth commuting. Access to several acclaimed schools. Inside youll find high ceilings balanced by hardwood flooring, carpeting, & tile. Great floor plan bathed in light, perfect for hosting & everyday dwelling. The living room is spacious w/ an additional family room. The dining room offers scenic views of the hills. The well-equipped kitchen features high end appliances from brands such as Viking, Sub-Zero, & more plus, a center island w/ more built-in appliances. At the end of a long day you can retire to one of several comfortable bedrooms. The luxurious primary has a pristine ensuite bathroom & large custom closet. The private backyard is wide w/ a deck & grassy lawn. If home is where the heart is, this home is sure to capture yours

19 Mirasol CT, Hillsborough

$9,980,000

6 Beds ⋅ 8 Baths ⋅ ML81929424 MLS

Magnificent Mediterranean Estate with 6 bedrooms, 6 bathrooms, plus an additional two half bathrooms/Soaring ceilings with custom skylights provide an abundance of natural lighting over the dramatic entry that features grand columns and graceful staircases with custom ironwork and a cascading water wall feature/Spacious Primary bedroom with high coffered ceiling, bold crown molding, fireplace, a separate walk-in closets and spacious main bathroom that features a large shower with dual heads and a separate tub/Sizable office/study with cozy fireplace and built-in bookshelves that are blessed with an abundance of natural lighting from multiple sides/The resort-style backyards is perfect for entertaining and relaxing. Dramatic views of San Francisco Bay and beyond can be enjoyed from the spacious terraces and patio that surround the huge refreshing pool and jacuzzi. Other feathers include a sports court, water fountains, fireplace, and fire pit. A spacious gated driveway and 3-car garage.

38 Lemon CT, Hillsborough

$3,700,000

4 Beds ⋅ 3 Baths ⋅ ML81929269 MLS

This classic contemporary home enhances the owner's daily routine: four large bedrooms, a beautiful bathroom, formal foyer, living room, and dining room provide residents with peace and quiet. Beautiful hardwood and tile flooring throughout the home. The kitchen has a great room concept with a dining area and adjoining family room. The appliances are also equipped to good specifications. A central vacuum system and convenient hallway laundry make indoor care easy, and the 3-car garage has custom built-in cabinets for all your storage needs. The property is ideal for family and friends gatherings indoors and out. Gently sloping grounds with fruit trees, terraces, and evergreens complete the image of this tranquil setting. Hillsborough schools are just a short distance away and shopping and highway access are convenient.

50 W Avondale RD, Hillsborough

$7,250,000

5 Beds ⋅ 6 Baths ⋅ ML81929010 MLS

Elegance abounds in this original William Wurster design that was expanded and restored to perfection by renowned local architect Farro Essalat. Tucked away on approximately .73 acres of outstanding, verdant grounds, 989 Hayne Road is a rare gem that is to be cherished for generations to come. Every feature of this five bedroom, five and one-half bath home offers the highest level of design, impeccable attention to detail, and masterful craftsmanship. The welcoming foyer with beautiful curved staircase is a fitting prelude to the grandly-proportioned interior spaces, which include a library, billiard room, huge family room and mud room. The delightful flow of this exceptional home extends to the incredibly manicured grounds, offering beautiful planter beds, tranquil garden pathways, a rose garden, fire pit, superb outdoor kitchen, and spa with beautiful views. This magnificent estate presents a unique opportunity for the discerning owner seeking that special, one-of-a-kind property.

989 Hayne RD, Hillsborough

$12,700,000

5 Beds ⋅ 5 Baths ⋅ ML81927136 MLS

Nestled in Lower North Hillsborough, sits this stately traditional-style 6,000+/-square foot home located in Prestigious Fagan Estates. This stunning five bedroom, four and two half bath estate features an expansive living and dining room with grand picture windows and an abundance of natural light, a large family room and a contemporary kitchen. In addition, enjoy a wood-paneled library, a separate office and an amazing indoor/outdoor glass-enclosed pavilion that overlooks a nearly half-acre Japanese garden. There is room for all with an expansive first-floor primary suite with a sitting area and plenty of closet space. Four additional bedrooms complete this home. The rear Japanese Garden was designed by Renowned Landscape Architect Katsuo Saito. Enjoy over 20 heritage trees including Cut Leaf Maples and Black and Red Pine Trees and numerous anchor stones throughout the garden. An iconic 10,000-bottle wine cellar, temperature controlled at 48 degrees and humidity controlled at 70%.

30 Fagan DR, Hillsborough

$4,888,888

4 Beds ⋅ 5 Baths ⋅ 423741967 MLS

Welcome to the elegance of a bygone era at 575 Hayne Road in the prestigious Hillsborough Heights neighborhood. Built in 1929 by famed architect Albert L. Farr, this exceptional estate boasts a true "storybook" feel and olde-worlde charm in the Cotswold style. Nestled on a 25,700 sq.ft. lot filled with gorgeous landscaping and mature redwood trees, the home's exterior has handsome redwood siding and brickwork facades, draped with sumptuous wisteria and ivy. The main level features a spacious living room, formal dining room, eat-in kitchen, au-pair bonus room, office bonus room, and large playroom. Multiple French doors afford a wonderful flow from the lush front garden to the expanse of the back patio. The upper level has four bedrooms including a grand primary suite, plus a sunny bonus room with a balcony. The serene backyard has verdant foliage, a large deck, brick patio, wandering walking paths, hot tub, plus a separate vegetable and flower garden. This magnificent estate presents a rare opportunity for the discerning owner seeking a one-of-a-kind property.

575 Hayne Road, Hillsborough

$28,000,000

9 Beds ⋅ 9 Baths ⋅ ML81928072 MLS

Remember the old, tired Fagan Estates Mansion? NEW LIFE HAS TRANSFORMED THIS HOME INTO A ONE-OF-A-KIND MODERNIZED SMART-HOME MANSION! THE IMPOSSIBLE WAS JUST DONE W/ THESE MULTI-MILLION DOLLAR RENOVATIONS! This magnificent estate perfectly integrates timeless architecture w/ a modern interior, brimming w/ top-of-the-line amenities. An estate fit for royalty! Interior has 100s of recessed smart lighting, smart thermostats w/ AC, motorized hunter Douglas, & Sonos speakers throughout; all controlled by a smart phone. BRAND NEW & MODERNIZED KITCHEN & 8.5 NEW BATHROOMS. Highlights include 8 new HVACs, majestic stained-glass windows, artisan stone grand fireplaces, high ceilings, gorgeous living room, manicured landscaping, all windows w/ an extra layer of glass, guest parking for 30+, & SO MUCH MORE! Too many details to list, to see is to believe! Exterior was transformed while preserving the classic façade. Exterior has a sprawling green lawn & sparkling pool. Adjacent Lot also for sale.

85 Fagan DR, Hillsborough

$5,998,000

5 Beds ⋅ 4 Baths ⋅ ML81927965 MLS

SONOMA FARMHOUSE: READY FOR GAME DAY! Wow Factor opportunity for Hillsborough's most exciting and dynamic indoor/outdoor lifestyle! All remodeled inside and out at the very best cul-de-sac in prestigious Lakeview! Meet, Mingle, Fun in the Sun, from Coffee to Cocktails, Super Bowl Parties, All Day on the Sport Court, Grill and Chill, Easter Egg Hunts, the best play dates ever, Margaritas never tasted better, Take a Deep Breath in a cozy chair by the Firepit...It's all here! Super-smooth modern floorplan of 3,670 sq. ft. flows mostly on one level from indoors to outdoors, with 4 beds on the main level together, plus upper level for teen suite, hobbies/5th bed. Bling factors of remodeled kitchen Wolf, Sub-Zero, 2 Thermador dishwashers,12 ft. ceiling, plus the Primary Suite with huge walk-in closet & decadent bathroom. World-class entertaining pavilion of outdoor kitchen, 42-inch Lynx Grill & more. Flat lawns in sunny privacy on .56 Acre, 100% usable, plus a pro full sport court @ side

30 Buckingham CT, Hillsborough

$3,988,000

5 Beds ⋅ 3 Baths ⋅ ML81927948 MLS

Don't miss this beautiful home located in the most exclusive area of the SF Bay 2.0 acre lot - Featuring 5 bedrooms and 3 bathrooms , Kitchen space with black onyx granite countertop. The expansive terrace and deck area welcomes outdoor entertaining surrounded by partial views of the Bay. Enjoy a massive main-floor owner's suite offering terrace/deck access.Relax in the large living room or entertain in the dining area surrounded by a two-sided fireplace and access to terrace/deck area.With high ceilings, exposed beams and floor to ceiling windows in both the living and dining areas.Five Large Bedrooms, newly remodeled baths are grouped together on one level, one of bedrooms shown as an office in pictures. Primary bedroom with plenty of natural light,New homes are being built on the street which could increase the value of this home over the next few years. Secluded from everyday street traffic.

1232 Kenilworth RD, Hillsborough

$7,500,000

ML81927922 MLS

LIFE AT THE TOP: HILLSBOROUGH'S MOST EXCITING NEW DESIGN! At the intersection of light, vistas, and design prowess, we embrace this innovative composition overlooking the Bay. Marin County architect Brooks McDonald fuses organic materials and clean lines that speak to the strength of this North Hillsborough knolltop. Destined to be a masterwork in the Transitional genre, your chance to acquire the land & ADRB-approved plans, ready to be built to your vision. Luxe inspirations of legendary Southern California architects Scott Mitchell & Paul McClean, resort flair. Hillsborough's most exciting new design, now awaits curated construction by local artisan Nejasmich Developments. *Price is for Land & ADRB-Approved Plans *5 beds, 5.5 baths, 2-Story Lobby * Stunning 2-Story Indoor/Outdoor Great Room ceilings soaring to nearly 20 feet! *Zen-Spa Primary Bath Opens to Bay-View Terrace * Main house is 6,240 + 543 foot detached ADU = 6,783 feet brand new luxury. 3-car garage is an added 909 feet.

55 Del Monte DR, Hillsborough

$12,888,000

6 Beds ⋅ 8 Baths ⋅ ML81927333 MLS

HILLSBOROUGH'S SKY PALACE...An unrivaled Bay-View mansion within 15 minutes of SFO airport. This opulence and scale are rarely seen! Glamorous Jetliner vistas above the Bay, San Mateo Bridge, airplanes touching down, and glittering lights. Built new less than 6 years ago, the architecture centers around a Royal 3-Story Staircase that soars over 30 feet above. Surely one of the most epic entries in all of Town, & the perfect pivot to every grand living space you can imagine on 3 levels. The 2nd (main) level showcases Bay-view entertaining with morning sun from the east for your huge luxury kitchen (with 10 ft. ceilings) & family room. The Bay-View terrace is like an outdoor living room for all party seasons. No luxury is spared from room to room: 6 beds, 7 full baths, CEO Office, Ultra-Luxe Primary Suite, Top Floor family quarters w/ mezzanine media lounge. Wine tasting room, gym, billiards, sauna, au pair/in-law, home theater!

101 Bella Vista DR, Hillsborough

$7,500,000

5 Beds ⋅ 6 Baths ⋅ ML81927240 MLS

LIFE AT THE TOP: HILLSBOROUGH'S MOST EXCITING NEW DESIGN! At the intersection of light, vistas, and design prowess, we embrace this innovative composition overlooking the Bay. Marin County architect Brooks McDonald fuses organic materials and clean lines that speak to the strength of this North Hillsborough knolltop. Destined to be a masterwork in the Transitional genre, your chance to acquire the land & ADRB-approved plans, ready to be built to your vision. Luxe inspirations of legendary Southern California architects Scott Mitchell & Paul McClean, resort flair. Hillsborough's most exciting new design, now awaits curated construction by local artisan Nejasmich Developments. *Price is for Land & ADRB-Approved Plans *5 beds, 5.5 baths, 2-Story Lobby * Stunning 2-Story Indoor/Outdoor Great Room ceilings soaring to nearly 20 feet! *Zen-Spa Primary Bath Opens to Bay-View Terrace * Main house is 6,240 + 543 foot detached ADU = 6,783 feet brand new luxury. 3-car garage is an added 909 feet.

55 Del Monte DR, Hillsborough

$7,450,000

4 Beds ⋅ 4 Baths ⋅ ML81907080 MLS

Located on one of Hillsborough's most sought after streets, this remodeled and expanded single level English Country home is at home and in harmony with its natural environment affording incredible privacy and serenity within the sanctuary of heritage Oaks, Blue Pines and Redwood trees. The magnificent setting boasts formal grounds, brick and cobblestone walls, English country window boxes and an array of flora and fauna perfect for grand entertaining and relaxed daily living. All usable .84 AC lot bursting with color and fragrance throughout the year complete with a sparkling Pool/Spa with a Shamu deck. Luxurious Primary Suite with an intimate sitting room with Oak bookshelves, dual Fireplace, separate double vanities and jetted tub. Open and Airy formal Living Room and Dining Room with beautiful views of the rear grounds. Professionally-equipped culinary Kitchen with custom Alder wood cabinets, Mahogany Enkeboll moldings and top of the line Thermador and Sub Zero appliances.

2045 FOREST VIEW AVE, Hillsborough

$13,500,000

6 Beds ⋅ 9 Baths ⋅ ML81926528 MLS

Nestled on a gated and lushly landscaped 1 acre lot, this custom built north Hillsborough estate showcases a rare combination of luxury and casual elegance. Offering 6 bedroom suites, incl. 2 primaries, with one on the first floor. Impeccably maintained, this home boasts a formal living and dining rooms, and wood paneled office. The gourmet kitchen offers a calacutta marble center island, professional grade appliances and adjacent family room which opens to a spacious patio. The lower level of this home features a media room, exercise area, and wine cellar. Au pair quarters round out the living spaces. The elevated central courtyard can be accessed from several rooms and opens to the newly added heated pool, rose bushes, oak trees, and oversized fire pit. Additional features include gas powered generator, sonos system, updated landscaping and irrigation, (8) camera security system, radiant heating, and multi-zone air conditioning, (5) fireplaces, (4) car garage, and room for an ADU.

33 Farm LN, Hillsborough

$7,250,000

5 Beds ⋅ 6 Baths ⋅ ML81926007 MLS

Welcome to this spacious family home on the highly sought after, Ascot Road. Entering into the foyer that leads to the large and bright common areas. The formal living and dining rooms include walls of glass that open to the beautifully landscaped private backyard. The chefs kitchen features a large island and is connected to the family room. The left wing of the house leads to four the oversized bedrooms suites. Upstairs youll find an office loft and grand master bedroom with sizable walk-in closet and bath. Designed around the yard, the backyard retreat features an expanded patio with fire pit, large grass lawn, and a pool/spa, perfect for entertaining. The yard also features a built-in outdoor kitchen/BBQ. Just a couple minute drive to downtown Burlingame and San Mateo, this impeccable home is ready for its next family!

302 Ascot RD, Hillsborough

$2,888,000

3 Beds ⋅ 3 Baths ⋅ ML81926324 MLS

HUGE PRICE REDUCTION !!!!!!!!!!! Wow! Right as you enter you will be greeted by spacious living quarters w/ high ceilings, an ideal floorplan, & craftsman style details such as tasteful wood ceilings. Much of this home offers scenic views of the backyard, a space reminiscent of a forest w/ lots of mature trees & a peaceful stream. The backyard offers several decks w/ plenty of space for the adults to host loved ones or to relax & mediate by your own private serene stream. And for the kids, lots of space to play & explore amongst the trees. Inside, large windows abound bathing the floorplan in natural light. The living room is more than accommodating. The kitchen has stainless steel appliances w/ the dining room just around the corner. All the bedrooms are a peaceful retreat w/ the primary featuring a balcony overlooking the backyard & ensuite bathroom. Seller reserve the right to reject any offers. There's also a family room w/ sliding glass doors leading out to another deck.

453 Remillard DR, Hillsborough

$14,900,000

5 Beds ⋅ 6 Baths ⋅ ML81926309 MLS

This opulent estate in the Carolands area spans 2 acres. The grand foyer leads you to a light-filled formal living room complete with high ceilings and a fireplace. The gourmet kitchen will help you prepare for hosting luncheons and dinners in the elegant banquet room. Afterwards, you could proceed to the salon to unwind with cocktails and games. Move between floors in your very own elevator, use the wine cellar to store your collection, and set up to work remotely in the library. Relax during the afternoon or evening in one of the many spacious bedroom suites. The backyard includes a playground area and 1 bedroom guest house with lanai to live it up during the warmer seasons. Matured gardens make for delightful outdoor lounging or entertaining - enjoy the pool & spa or organize a tennis match with friends. Parking is plentiful with a 4 car garage and the expansive driveway prominently features a stately fountain.

3300 Ralston AVE, Hillsborough

$5,750,000

4 Beds ⋅ 5 Baths ⋅ ML81926267 MLS

Experience idyllic indoor-outdoor living in this tastefully renovated 4BD, 4.5BA Hillsborough home! Enhanced features, contemporary design, and a stunning open-concept interior have shaped it into an entertainer's paradise. Hardwood flooring, crisp white tones, and serene natural views create a welcoming ambiance throughout the 3,549 sqft layout. Sunlit and spectacular, the great room is warmed by a sleek linear fireplace flanked by stylish built-ins, and expansive glass sliders allow a seamless flow to your wraparound terraced gardens, sports court, and the large deck facing the airport and bay. The remodeled gourmet kitchen has upgraded stainless steel appliances and a multi-seater island. The primary ensuite's oversized shower and separate soaking tub immerse you in spa-like relaxation. Notable items include a den, private office, and detached 2-car garage with a bonus room. Come for a tour before the opportunity passes you by! Per County Records: SQFT is 3,230 & BA count is 4.

660 Pullman RD, Hillsborough

$7,488,000

4 Beds ⋅ 5 Baths ⋅ ML81925222 MLS

Introducing 333 Bridge Road, a stunning mid century modern masterpiece transformation. Located in prime Lower South Hillsborough, this premier property sits at the end of a cul-de-sac, offering unparalleled privacy. Boasting 4 bedrooms including a large primary retreat, 4.5 bathrooms and just under 4,300 sqft of living space. With wide white oak floors, walls of glass, and an open-concept design, this home is a true example of modern luxury. All new kitchen is equipped with Wolf, Cove, and Sub-Zero appliances. Additional features include a large media room, laundry room, powder room, and 4-zone heating / air conditioning. The level rear grounds include a solar-heated pool and separate spa, elevated terrace with fire pit, and drought-tolerant synthetic lawn bordered by terraced gardens. Conveniently located between San Francisco and Silicon Valley, with top rated schools, restaurants, and boutique shops. Experience luxury and California elegance at its finest!

333 Bridge RD, Hillsborough

$7,930,000

ML81926059 MLS

PRIME LOWER HILLSBOROUGH LOT WITH .90 ACRES OF USABLE LAND! NEWLY RENOVATED POWERFUL WATER WELL!!!! SAVE ON YOUR WATER BILLS WHEN WATERING YOUR GARDENS! YOU WILL NOT FIND A BETTER CHOICE THAN THIS CURRENTLY IN HILLSBOROUGH!!! Located at the end of an exclusive cul-de-sac in the prestigious historic Fagan Estates subdivision. This lot features A WIDE SPRAWLING GREEN LAWN with almost an acre of pristine land to BUILD YOUR DREAM HOME! Encompassed by an abundance of mature trees offering total privacy. Only .5 miles walking distance to bustling Downtown Burlingame. The lot offers the perfect canvas to get everything you've dreamed about with only your imagination being the limit. ONCE-IN-A-LIFETIME OPPORTUNITY, RARE LISTING, AND MORE!

90 Fagan DR, Hillsborough

$6,986,000

5 Beds ⋅ 5 Baths ⋅ ML81925578 MLS

Exclusive Luxury Property for Sale in Hillsborough - A Must-See! Experience unparalleled luxury and sophistication in one of Hillsborough's most sought-after locations. This exquisite property showcases the finest aspects of elegant living, nestled within an elite and well-maintained community. Boasting a generous 1.04 acre lot, this stunning home offers an exceptional lifestyle for discerning homeowners. This sophisticated home offers an exceptional lifestyle, featuring a seamless integration of the kitchen, dining, and living areas in the expansive great room. The luxurious master suite includes a roomy master bath and custom walk-in closet, while the open floor plan is bathed in natural light. The resort-like outdoor space boasts a sparkling pool, full-sized tennis court, and a spacious deck with a BBQ area and an additional dwelling unit (ADU) room. Don't miss the opportunity to embrace the distinguished and opulent lifestyle that awaits you in this must-see Hillsborough gem. Property Website: http://www.135bellavistadr.com/mls/98191256

135 Bella Vista DR, Hillsborough

$6,850,000

5 Beds ⋅ 6 Baths ⋅ ML81925515 MLS

Gracefully situated on a private and gated .70-acre lot, this majestic +/-5,860s.f. home offers grand-scale rooms in a seamless floor plan. Comprising 5 bedrooms & 6 full baths, this home is thoughtfully designed for today's lifestyle. Features include a stunning foyer, huge living room with a see-through fireplace adjoining the elegant formal dining room, a wood-paneled family room with fireplace, wet bar, custom bookcases, and a sliding glass door leading to the stunning rear grounds. The chef's kitchen with center island & breakfast nook with fireplace open to the amazing yard. A large office with fireplace, & incredible primary suite replete with marble fireplace, two walk-in closets, two bathrooms & dressing area are just a few of the highlights of this extraordinary home. The remarkable grounds feature large patios, a sweeping lawn, pool, enchanting pathways, and a large storage shed. This extraordinary property is truly the epitome of grandeur and elegance in the finest location

920 Vista RD, Hillsborough

$6,795,000

5 Beds ⋅ 6 Baths ⋅ ML81925497 MLS

A premier street in lower north Hillsborough is the setting for this architectural grande dame freshly updated and ready to move in or awaiting a further transformation into your own dream vision. Distinguished by the refined grace and character that comes only through the passage of time, this magnificent home dates to 1938 on an elevated street that presents San Francisco Bay views from the upper level. Vintage appointments that recall its early heritage are on display at every turn combined with fresh paint inside and out plus updates in the kitchen and all bathrooms. Fine hardwood floors unify the entire home, and expansive windows and glass doors fill the spaces with abundant light. The floor plan is ever so spacious spanning three levels with a traditional arrangement of 5 bedrooms upstairs plus a lower level with potential as an Accessory Dwelling Unit. Outside, old world glamour continues around the spacious pool and brick terrace along with a pool cabana with large spa and ample room for fitness or entertaining. The entire setting is abundantly private on a level lot of nearly one-half acre, plus this home has access to excellent Hillsborough schools.

468 El Centro RD, Hillsborough

$5,488,000

5 Beds ⋅ 4 Baths ⋅ ML81925349 MLS

Spanish elegance combined with modern amenities is what you will find at 2208 Oakdale in the desirable Hillsborough Oaks neighborhood. A long list of upgrades transformed this home into a contemporary haven! From the gated courtyard, step through the arched entry door to discover newly installed windows, recessed lighting, and refinished hardwood floors. Exuding a timeless elegance, the dining room has French doors to the patio. Widened doorways connect you to the family room with a fireplace and direct access to the backyard. Across its increased SQFT, the remodeled kitchen has top-of-the-line appliances and stunning hard surfaces. Well-sized bedrooms, including your luxurious primary suite, are accommodated by renovated baths. Enjoy the balcony overlooking lush grounds maintained by an automated sprinkler system. Outdoor lighting and an audio system set the mood for alfresco celebrations. Don't miss out on this gorgeous home! Per County Records: SQFT is 3,628 & BD count is 4.

2208 Oakdale RD, Hillsborough

$4,799,000

5 Beds ⋅ 6 Baths ⋅ ML81924830 MLS

Welcome home to 837 Chiltern Road. An Entertainers paradise with captivating views, oversized rooms and finishes befitting a custom hillside paradise in Hillsborough. Nestled on an approximate half acre hillside lot, this custom abode has low maintenance landscaping and several patio spaces for entertaining and gazing. Main level features gorgeous and timeless hardwood flooring, a formal living room with soaring tray ceiling, formal dining room with views, large kitchen with Island, and one of the multiple primary bedrooms. Upper level features an oversized primary bedroom with a private balcony and amazing views. The suite features a separate sitting room, two walk-in closets and two full bathrooms. Two additional oversized Jack and Jill bedrooms also share 2 full bathrooms. The lower level features 2 garages, a possible 3rd primary bedroom or 2nd family room as well as 2 wine storage areas.

837 Chiltern RD, Hillsborough

$9,985,000

4 Beds ⋅ 4 Baths ⋅ ML81924120 MLS

Cotswold Style with Contemporary Flair! Exceptional home by RG Developments has been crafted w/the highest quality materials, keen attention to detail & offers one the opportunity to own a timeless masterpiece. Classic style incorporating clean lines & robust spaces! Bluestone, Clinker brick, Bevolo gas lanterns, flora, & fauna... Bright and open floor plan; top of the line amenities: kitchen-eating area-family room w/ top-of-the-line appliances & an abundance of natural light. Main house feat: w/ 4BRs, huge primary retreat & ground floor BR suite, 3-1/2 BAs, private dining room, formal entry w/ adjacent living room, huge kitchen w/ eat-in area, expansive family room & 2nd floor office/media or 5th BR retreat. ADU feat: BR, full BA, kitchen w/ gourmet appliances, high ceilings, private/easy access. Plus: Speakeasy masterfully appointed bar w/ 1/2 Bath. Grounds feat. BBQ area, vegetable garden, spa, playgrounds, gated & private driveway, carefully selected planting & much much more!

2415 Summit DR, Hillsborough

$11,000,000

5 Beds ⋅ 7 Baths ⋅ ML81923674 MLS

2.5+ acre estate in the heart of Hillsborough! This architecturally magnificent gated estate is nestled at the end of long private driveway and is on the market for the first time in almost 50 years! Situated on secluded park-like grounds, this structure is a work of art featuring uninterrupted style and craftsmanship that blend an array of materials, unique finishes and unsurpassed woodwork throughout. Highlighting the integration of indoor and outdoor spaces, this house features a front courtyard, open loggia corridors, lofty timber-beamed ceilings, pool house and guest house, oversized pool, tennis court, al fresco dining patio, garden terraces, magical strolling paths and impeccable grounds.The main house is approx 6,310sf with 5 bed/5.5 baths; the two additional structures have a combined 1,000sf (approx) with 1bed/1bath. This Hillsborough home feels like you are away from it all even though it's just minutes from major freeways, Silicon Valley and San Francisco.

862 Chiltern RD, Hillsborough

$6,800,000

4 Beds ⋅ 3 Baths ⋅ ML81923312 MLS

Unique opportunity to buy, then build a 2 story California Craftsman with approve plans. Situated on a level .51 acre lot on one of Hillsboroughs most highly sought after streets in the Country Club Manor Neighborhood. Walking distance to award-winning Hillsborough Schools and Downtown Burlingame. Combining natural beauty and sophistication, this approachable and livable design shows impressive curb appeal with classic covered porches and refined millwork throughout. The approved plans consist of 5 spacious bedrooms, 4 bathrooms + 2 powder rooms spanning 4,663 sq. ft. of living space and a 1 bedroom, 1 bath +/-550 sq. ft. ADU. With ultimate polish and panache, and completely custom throughout, this home will captivate the most discerning of homeowners with the desire to build their dream home.

1950 Ralston AVE, Hillsborough

$3,598,000

4 Beds ⋅ 3 Baths ⋅ ML81922755 MLS

20 Shady LN, Hillsborough

$6,280,000

ML81922464 MLS

ONE OF THE BEST BAY VIEWS IN ALL OF HILLSBOROUGH! AN ABSOLUTE TREASURE & LANKMARK PROPERTY! These views MUST BE SEEN IN PERSON to truly admire, we mean it! Stunning unobstructed panoramic 270-degree+/- views as far as the eye can see, to the blue waters of the SF Bay & beyond! Enjoy breathtakingly vibrant sunsets & cool relaxing nights under the stars. Privacy & luxury are other hallmarks. You can go ahead & move right into this TURN-KEY RENOVATED home or use the preliminary architect drawn renderings of a new DREAM HOME. The move-in ready home offers scenic views from almost every room in the house, plus an open floor plan & premium renovations. The new dream house will sit in a new location way back, w/ a HUGE flat yard on the front & side. You get everything you could want, long driveway, total privacy, immaculate billion-dollar views, huge backyard, exclusive neighborhood & a home sure to impress everyone. Photos: https://greenbanker.com/255pinehill/ Tenant occupied dont drive in

255 Pinehill RD, Hillsborough

$6,280,000

3 Beds ⋅ 2 Baths ⋅ ML81922454 MLS

ONE OF THE BEST BAY VIEWS IN ALL OF HILLSBOROUGH! AN ABSOLUTE TREASURE & LANKMARK PROPERTY! These views MUST BE SEEN IN PERSON to truly admire, we mean it! Stunning unobstructed panoramic 270-degree+/- views as far as the eye can see, to the blue waters of the SF Bay & beyond! Enjoy breathtakingly vibrant sunsets & cool relaxing nights under the stars. Privacy & luxury are other hallmarks. You can go ahead & move right into this TURN-KEY RENOVATED home or use the preliminary architect drawn renderings of a new DREAM HOME. The move-in ready home offers scenic views from almost every room in the house, plus an open floor plan & premium renovations. The new dream house will sit in a new location way back, w/ a HUGE flat yard on the front & side. You get everything you could want, long driveway, total privacy, immaculate billion-dollar views, huge backyard, exclusive neighborhood & a home sure to impress everyone. Photos: https://greenbanker.com/255pinehill/ *Tenant occupied dont drive in.

255 Pinehill RD, Hillsborough

$7,650,000

5 Beds ⋅ 6 Baths ⋅ ML81920640 MLS

SECLUDED RESORT ESTATE with all the Grandeur of a Newer Modern Construction! Built New in 2001, discover Modern-Era Luxury with Charismatic Design. One of the very best blocks in the Carolands neighborhood, shouldered by mansions. 610 Pullman occupies the perfect spot in the neighborhood of minimal through-traffic and flat streets. The feeling of privacy and separation from neighbors is divine, showcased by a huge sunny yard, resort-like waterfall feature, giant rectangle pool and spa in glorious sunshine, and tons of space for kid's play structure or ADU. An impressive 5,740 sq. ft. spans three levels of living. *5 bedrooms, 5.5 bathrooms, CEO Library, plus lower level Rec Room ideal for Media, Gym, or even a 6th bedroom/Guest hideaway. *Awesome high ceilings *Smooth Modern Floorplan and Main Level Suite that acts as a Second Primary* Resort-style Pool/Spa, Space for Outdoor Kitchen, Vast Open Lawns.

610 Pullman RD, Hillsborough

$11,245,000

6 Beds ⋅ 7 Baths ⋅ ML81920512 MLS

CHATEAU NOUVEAU...nearly 9,000 feet of Contemporary Zeitgeist. Discover this Residential Work of Art at the very heart of Lower South Hillsborough. Architecture that designers dream of with towering ceilings, open flowing spaces, and bold, exciting statements in the modern vernacular. Imagine crafting a re-invented color palette, your minimalist interior design vision, or eclectic interpretation on a grand scale. 6 beds, 6.5 baths, Office, Gym, Screening Room, Recreation Room, Indoor/Outdoor Loggia, 4-car side-by-side garage, plus gated 2-car carport. This pancake-flat lot of .78 Acre is 100% usable and welcomes your new ADU/Pool House Ideas. Just steps to South School and the Hillsborough Racquet Club, this is a special location filled with history, prestige, and utmost convenience. *Seller may entertain Seller Financing to Qualified Buyers*

2 Homs CT, Hillsborough

$4,495,000

4 Beds ⋅ 4 Baths ⋅ ML81919182 MLS

Spacious sun-drenched living quarters & elegant amenities converge to create the perfect quintessential Hillsborough home. This corner-lot estate is emanating w/ thoughtful design choices & functional appointments. Tasteful hardwood flows throughout this open floor plan, complemented by crown molding, tall ceilings, recessed lighting, & wide windows. The myriad of windows opens this home up to lots of natural light creating an open airy ambiance. The floorplan is ideal for routine living & hosting. The stylishly appointed kitchen is equipped w/ all high-end appliances. The dining room & living room connect by way of open concept, perfect for entertaining. The family room has a custom bar, half bath, & access to the backyard. All the bedrooms are a welcome retreat after a long day. The pristine bathrooms feature double vanities. The cherry on top is the backyard with a sparkling pool, big lawn, & pickleball / multi-use sports court. Minutes from Dwntwn San Mateo & sought-after schools.

1055 Woodland DR, Hillsborough

$15,750,000

5 Beds ⋅ 7 Baths ⋅ ML81918112 MLS

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard hall, and the "Morocco Room" lounge. Upstairs, the large master suite enjoys equally stunning views of the bay, in addition to a luxury spa bath and formal sitting room. A separate in-law suite and wine cellar with tasting room are located on the lower level of the residence. Equally impressive are the surrounding grounds, fully landscaped with grand-scale trees, expanses of manicured lawn, and an elevated terrace overlooking the views and swimming pool. All of this just minutes from shopping, dining, golfing, parks, and top rated Hillsborough schools. (Square Footage Per County Records: 8,629)

3085 Ralston AVE, Hillsborough

$7,999,000

6 Beds ⋅ 8 Baths ⋅ ML81918069 MLS

Timeless character & architecture awaits w/ an impressive 7,600 SqFt of living space. Taking cues from the neighborhood, this home offers total privacy & lots of verdant foliage. Quality craftsmanship takes center stage in this one-of-a-kind tutor abode. The wide-open & airy ambiance this floor plan offers is the perfect platform for both entertaining on a grand scale & everyday living. High ceilings, hardwood, crown molding, custom fireplaces, a grand staircase, tall windows, & intricate design elements can be found throughout. Expansive living quarters on multiple levels & two separate kitchens make way for plenty of room for you & your family/guests. Aspects include a fully equipped kitchen, huge formal dining room, custom library, grand office, a master suite fit for royalty, 2 decks w/ BREATHTAKING PANORAMIC SF BAYVIEWS, two living rooms & MORE! Private backyard oasis w/ a sparkling pool & lush lawn. Walking distance to Downtown Burlingame / North Elementary & Crocker Middle.

446 El Arroyo RD, Hillsborough

$5,989,000

5 Beds ⋅ 5 Baths ⋅ ML81917977 MLS

REMODELED THROUGHOUT MOST, COMPLETED IN 2023. The BEST location with a HUGE flat three-quarter-acre lot with usable land. One of the best deals you can possibly find in Hillsborough. The lot features sprawling lawns, a sparkling pool, & total privacy. Lots of space to play and entertain with the whole family. Minutes from Downtown Burlingame & prestigious schools. This Monterey Colonial has been totally transformed. Luxurious finishes can be found all throughout. Excellent floor plan overflowing w/ natural light from large windows & skylights. Host with ease. Well-sized living room & kitchen / family room. The NEW modern kitchen is constructed with high-end appliances. All the spacious bedrooms are en-suite with NEW pristine bathrooms & new closets. Lower level can be a home gym / play room / entertainment room. Home office and laundry room. Most lights controlled by smart features. Brand new heater. TOO MANY DETAILS, the list goes on and on. Take advantage of this rare opportunity.

1254 San Raymundo RD, Hillsborough

$68,000,000

8 Beds ⋅ 10 Baths ⋅ ML81917533 MLS

GREAT OPPORTUNITY FOR THIS TROPHY ESTATE***If you are looking for the best of the best, this is a once-in-a-lifetime opportunity for you to enjoy your life! After years of renovations, 1868 Floribunda Avenue is ready for you to view! The lot is almost 5x bigger than standard lots, all usable! Renovated to the highest quality, situated in one of the best locations in Hillsborough! Nearly 20,000 square feet throughout 6 buildings. New custom-built water well. Three private gates - resident driveway, guest driveway, and pedestrian walkway. No expense was spared for this property to reach the ultimate heights in a smart & secure dream home! You have to see it, to believe it! Qualified buyers only; qualifications requested in order to be screened before showings.

1868 Floribunda AVE, Hillsborough

$5,148,000

4 Beds ⋅ 4 Baths ⋅ ML81916302 MLS

Spacious & elegant, this Hillsborough beauty showcases luxury interior design complimented by gorgeous outdoor living. The grove of heritage olive trees beckons as you enter the spectacular courtyard with its rose garden, calming fountain & private patio. Anchoring the home is the remodeled kitchen with Carrara marble counters, custom cabinetry, stainless steel appliances, Wolf range & artisan tile. The living & family rooms are each warmed by a brick fire place. Step inside the fabulous butler pantry & attractive mudroom conveniently situated next to the large 3 car garage. Outside, a magical oasis awaits with the expansive backyard featuring fresh landscaping, new lawn, a pool, spa, & sport court with separate patio areas on the oversized .64 acre lot. This stunning Hillsborough home is close by downtown San Mateo & Burlingame with a variety of popular outdoor cafes, restaurants & shopping. Excellent schools and easy access to highways, Caltrain, Bart, & S.F. Airport.

10 Percheron PL, Hillsborough

$4,264,900

4 Beds ⋅ 4 Baths ⋅ CRIV23006272 MLS

Dream a little dream in Hillsborough, California. Seize the moment on this estate. Great size home on large lot approximately 25,200 square feet. This is a great opportunity to put your finishing touches on this gem. Don't miss this unique chance to say ''hello'' to your new dream getaway! All potential buyers are asked to check with City, County, Zoning, Tax, and other records to determine all details on this property listed above to their satisfaction. This is an AS-IS REO property.

75 Tobin Clark DR, Hillsborough

$6,888,000

5 Beds ⋅ 7 Baths ⋅ ML81915841 MLS

The bright, flowing indoor floorplan has been tastefully updated and is move-in ready. The home carries the dual-pedigree of San Francisco design pioneers architect Gardner Dailey and famed landscape architect Thomas Church. The indoor living areas naturally extend through French doors from the spacious main hall into a landscape of ambling paths under mature oaks, welcoming rose gardens, and shaded lawns. The circular terraces and circular Emerald pool are signature Church design elements as featured in Architectural Forum magazine and two Thomas Church books.

711 Hayne RD, Hillsborough

$3,488,000

5 Beds ⋅ 5 Baths ⋅ ML81898890 MLS

One-of-a-kind corner-lot Mediterranean-inspired estate that is seated on a generous 16,450 sqft lot. Located in the sought-after neighborhood of Hillsborough Park. This 3 story home shows off stunning architectural aesthetics w/ tall white columns, spectacular arches, terracotta accents, wrought iron elements, & more! Inside this house, you will be greeted by a cozy fireplace, high ceilings, exposed ceiling beams/truss that add a dramatic sense of strength & heft to the living room. This house has a spacious kitchen, formal dining, & breakfast nook. There is a family room that can be found in the basement, & this house has a space for a potential laundry room. There are 3 master suites upstairs, 1 bd on the main level & 1 on the lower level of the house. This home has plenty of windows throughout the entire house that brings in an abundance of natural light. Huge & Extra wide manicured lawns w/ plants & trees are found at both the front/rear exterior of this home w/ a large side patio. HUGE PRICE REDUCTION!!!!

1101 Black Mountain RD, Hillsborough

$14,999,000

6 Beds ⋅ 5 Baths ⋅ ML81898893 MLS

Over 1.8 acres, every square foot totally level, A perfect rectangle, Subdividable into 2 lots. One of only a few parcels of this size and quality in all of Hillsborough. Located in the most desirable location of lower Hillsborough among of some of Hillsborough's most beautiful estates. The perfect building site. When gone there will be no others.

210 Uplands DR, Hillsborough

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